ES2902390T3 - Derivados de imidazol condensados sustituidos por grupos hidroxi terciarios como inhibidores de PI3K-gamma - Google Patents

Derivados de imidazol condensados sustituidos por grupos hidroxi terciarios como inhibidores de PI3K-gamma Download PDF

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Publication number: ES2902390T3
Authority: ES; Spain
Prior art keywords: alkyl; membered; cycloalkyl; heterocycloalkyl; haloalkyl
Prior art date: 2017-10-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES18797408T

Other languages

English (en)

Spanish (es)

Inventor

Brent Douty

Andrew W Buesking

David M Burns

Andrew P Combs

Nikoo Falahatpisheh

Ravi Kumar Jalluri

Daniel Levy

Padmaja Polam

Lixin Shao

Stacey Shepard

Artem Shvartsbart

Richard B Sparks

Eddy W Yue

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Incyte Corp

Original Assignee

Incyte Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2017-10-18

Filing date

2018-10-17

Publication date

2022-03-28

2018-10-17 Application filed by Incyte Corp filed Critical Incyte Corp

2022-03-28 Application granted granted Critical

2022-03-28 Publication of ES2902390T3 publication Critical patent/ES2902390T3/es

Status Active legal-status Critical Current

2038-10-17 Anticipated expiration legal-status Critical

Links

239000003112 inhibitor Substances 0.000 title description 4
102100036052 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform Human genes 0.000 title description 2
101710096503 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform Proteins 0.000 title description 2
150000002460 imidazoles Chemical class 0.000 title description 2
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 1761
125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 465
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 454
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 386
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 380
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract description 306
125000001424 substituent group Chemical group 0.000 claims abstract description 303
125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 276
-1 aminosulfonylamino Chemical group 0.000 claims abstract description 223
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 194
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims abstract description 193
125000005843 halogen group Chemical group 0.000 claims abstract description 184
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 182
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 158
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 136
229910052805 deuterium Inorganic materials 0.000 claims abstract description 130
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 127
229910052799 carbon Inorganic materials 0.000 claims abstract description 106
125000003545 alkoxy group Chemical group 0.000 claims abstract description 101
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 100
125000006721 (C5-C10) heteroaryl (C1-C6) alkyl group Chemical group 0.000 claims abstract description 92
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 86
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 78
125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims abstract description 77
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 76
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 72
125000006598 aminocarbonylamino group Chemical group 0.000 claims abstract description 71
125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 60
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 59
101150073096 NRAS gene Proteins 0.000 claims abstract description 50
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 43
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 43
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 43
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 41
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 40
125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims abstract description 40
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 39
125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 37
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 35
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract description 35
150000001875 compounds Chemical class 0.000 claims abstract description 35
229910052702 rhenium Inorganic materials 0.000 claims abstract description 35
125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims abstract description 34
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims abstract description 32
150000003839 salts Chemical class 0.000 claims abstract description 32
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 31
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 26
125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 claims abstract description 23
229910052731 fluorine Inorganic materials 0.000 claims abstract description 21
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 17
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
229910052736 halogen Inorganic materials 0.000 claims abstract description 16
150000002367 halogens Chemical class 0.000 claims abstract description 16
125000003118 aryl group Chemical group 0.000 claims abstract description 15
229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
125000000304 alkynyl group Chemical group 0.000 claims abstract description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
125000006413 ring segment Chemical group 0.000 claims abstract description 9
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 7
101150107341 RERE gene Proteins 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
206010028980 Neoplasm Diseases 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
210000004027 cell Anatomy 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
201000011510 cancer Diseases 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
210000001744 T-lymphocyte Anatomy 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 7
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 7
206010039491 Sarcoma Diseases 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 5
230000014509 gene expression Effects 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
208000023275 Autoimmune disease Diseases 0.000 claims description 4
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 claims description 4
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
230000004770 neurodegeneration Effects 0.000 claims description 4
208000015122 neurodegenerative disease Diseases 0.000 claims description 4
201000002528 pancreatic cancer Diseases 0.000 claims description 4
208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 3
208000024172 Cardiovascular disease Diseases 0.000 claims description 3
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
206010006187 Breast cancer Diseases 0.000 claims description 2
208000026310 Breast neoplasm Diseases 0.000 claims description 2
206010018364 Glomerulonephritis Diseases 0.000 claims description 2
206010020751 Hypersensitivity Diseases 0.000 claims description 2
206010020772 Hypertension Diseases 0.000 claims description 2
208000007766 Kaposi sarcoma Diseases 0.000 claims description 2
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
206010033645 Pancreatitis Diseases 0.000 claims description 2
102000001253 Protein Kinase Human genes 0.000 claims description 2
230000002159 abnormal effect Effects 0.000 claims description 2
208000026935 allergic disease Diseases 0.000 claims description 2
230000007815 allergy Effects 0.000 claims description 2
208000006673 asthma Diseases 0.000 claims description 2
230000001363 autoimmune Effects 0.000 claims description 2
230000001413 cellular effect Effects 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
201000005202 lung cancer Diseases 0.000 claims description 2
208000020816 lung neoplasm Diseases 0.000 claims description 2
201000001441 melanoma Diseases 0.000 claims description 2
201000006417 multiple sclerosis Diseases 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
108060006633 protein kinase Proteins 0.000 claims description 2
206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims description 2
208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 8
206010025323 Lymphomas Diseases 0.000 claims 7
206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims 4
208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 4
201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims 4
201000009020 malignant peripheral nerve sheath tumor Diseases 0.000 claims 4
208000029974 neurofibrosarcoma Diseases 0.000 claims 4
AIJMGQDXUVKDIN-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,3-trifluoro-2-hydroxypropanamide Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C)C(C(=O)N)(C(F)(F)F)O AIJMGQDXUVKDIN-UHFFFAOYSA-N 0.000 claims 3
206010073478 Anaplastic large-cell lymphoma Diseases 0.000 claims 3
201000003076 Angiosarcoma Diseases 0.000 claims 3
208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 3
208000011691 Burkitt lymphomas Diseases 0.000 claims 3
208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 3
208000032004 Large-Cell Anaplastic Lymphoma Diseases 0.000 claims 3
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 3
206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 3
208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
208000001258 Hemangiosarcoma Diseases 0.000 claims 2
201000004331 Henoch-Schoenlein purpura Diseases 0.000 claims 2
206010019617 Henoch-Schonlein purpura Diseases 0.000 claims 2
241000711549 Hepacivirus C Species 0.000 claims 2
208000031814 IgA Vasculitis Diseases 0.000 claims 2
208000006404 Large Granular Lymphocytic Leukemia Diseases 0.000 claims 2
208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 2
208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
208000031839 Peripheral nerve sheath tumour malignant Diseases 0.000 claims 2
208000007048 Polymyalgia Rheumatica Diseases 0.000 claims 2
206010043540 Thromboangiitis obliterans Diseases 0.000 claims 2
206010047115 Vasculitis Diseases 0.000 claims 2
208000003455 anaphylaxis Diseases 0.000 claims 2
208000007502 anemia Diseases 0.000 claims 2
HWNHQKGIFMHZHG-UHFFFAOYSA-N imidazo[1,2-a]pyrazine-6-carboxamide Chemical compound NC(=O)c1cn2ccnc2cn1 HWNHQKGIFMHZHG-UHFFFAOYSA-N 0.000 claims 2
208000015446 immunoglobulin a vasculitis Diseases 0.000 claims 2
208000028867 ischemia Diseases 0.000 claims 2
208000003747 lymphoid leukemia Diseases 0.000 claims 2
201000005962 mycosis fungoides Diseases 0.000 claims 2
208000010721 smoldering plasma cell myeloma Diseases 0.000 claims 2
208000011580 syndromic disease Diseases 0.000 claims 2
230000009885 systemic effect Effects 0.000 claims 2
AKVKBTWZKYWPNV-UHFFFAOYSA-N 1,1-difluoropropan-2-ol Chemical compound CC(O)C(F)F AKVKBTWZKYWPNV-UHFFFAOYSA-N 0.000 claims 1
FYTNDBMJFQRFBF-UHFFFAOYSA-N 1-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1-cyclopropyl-2,2,2-trifluoroethanol Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)(F)F)(O)C1CC1 FYTNDBMJFQRFBF-UHFFFAOYSA-N 0.000 claims 1
ZTKSBSDLRDQGEC-UHFFFAOYSA-N 1-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-2,2,2-trifluoro-1-(1-methyltetrazol-5-yl)ethanol Chemical compound CN1N=NN=C1C(O)(C1=CC(C2=CN=C3N2C=C(N=C3N)C(F)(F)F)=C(C)C=C1)C(F)(F)F ZTKSBSDLRDQGEC-UHFFFAOYSA-N 0.000 claims 1
CNLZOTQYVVBAGU-UHFFFAOYSA-N 1-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-2,2,2-trifluoroethanol Chemical compound CC1=C(C=C(C=C1)C(O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C(F)(F)F CNLZOTQYVVBAGU-UHFFFAOYSA-N 0.000 claims 1
JJFCMBOEXQORLM-UHFFFAOYSA-N 1-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-2-fluorocyclopentan-1-ol Chemical compound CC1=C(C=C(C=C1)C1(O)CCCC1F)C1=CN=C2N1C=C(N=C2N)C(F)(F)F JJFCMBOEXQORLM-UHFFFAOYSA-N 0.000 claims 1
UPOQEQFRJRHVGQ-UHFFFAOYSA-N 1-[8-amino-3-[2-methyl-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]piperidin-4-ol Chemical compound C=12C(=NC(=CN2C(=CN=1)C1=C(C)C=CC(C(O)(C)C(F)(F)F)=C1)N1CCC(CC1)O)N UPOQEQFRJRHVGQ-UHFFFAOYSA-N 0.000 claims 1
VQOIAIVUVLWSIK-UHFFFAOYSA-N 1-[8-amino-3-[5-(1,1-difluoro-2-hydroxypropan-2-yl)-2-methylphenyl]imidazo[1,2-a]pyrazin-6-yl]piperidine-4-carbonitrile Chemical compound NC=1C=2N(C=C(N=1)N1CCC(CC1)C#N)C(=CN=2)C1=C(C=CC(=C1)C(C(F)F)(C)O)C VQOIAIVUVLWSIK-UHFFFAOYSA-N 0.000 claims 1
YEVUBSDDZZVRCS-UHFFFAOYSA-N 2-[3-(8-amino-6-methylimidazo[1,2-a]pyrazin-3-yl)-4-methylphenyl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)(F)F)(C)O YEVUBSDDZZVRCS-UHFFFAOYSA-N 0.000 claims 1
YJQYZDDVSHYRLY-UHFFFAOYSA-N 2-[3-(8-amino-6-pyrimidin-5-ylimidazo[1,2-a]pyrazin-3-yl)-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C=1C=NC=NC=1)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(C)O YJQYZDDVSHYRLY-UHFFFAOYSA-N 0.000 claims 1
YLBRSNLIYLCHDR-UHFFFAOYSA-N 2-[3-[4-[8-amino-3-[5-(1,1-difluoro-2-hydroxypropan-2-yl)-2-methylphenyl]imidazo[1,2-a]pyrazin-6-yl]pyrazol-1-yl]-1-(cyclobutanecarbonyl)azetidin-3-yl]acetonitrile Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)F)C1=CN=C2N1C=C(N=C2N)C1=CN(N=C1)C1(CC#N)CN(C1)C(=O)C1CCC1 YLBRSNLIYLCHDR-UHFFFAOYSA-N 0.000 claims 1
OGQRFUWIBQYXPY-UHFFFAOYSA-N 2-[3-[8-amino-6-(1,2,4-triazol-1-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)F)C1=CN=C2N1C=C(N=C2N)N1C=NC=N1 OGQRFUWIBQYXPY-UHFFFAOYSA-N 0.000 claims 1
SEPRRBCVLDCSAX-UHFFFAOYSA-N 2-[3-[8-amino-6-(1,3-dimethylpyrazol-4-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CN1C=C(C(C)=N1)C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)F SEPRRBCVLDCSAX-UHFFFAOYSA-N 0.000 claims 1
BSTVRXOSASBKDQ-UHFFFAOYSA-N 2-[3-[8-amino-6-(1,3-oxazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,3-trifluoropropane-1,2-diol Chemical compound NC=1C=2N(C=C(N=1)C1=CN=CO1)C(=CN=2)C=1C=C(C=CC=1C)C(CO)(C(F)(F)F)O BSTVRXOSASBKDQ-UHFFFAOYSA-N 0.000 claims 1
ACOIHWFRGXUVFL-UHFFFAOYSA-N 2-[3-[8-amino-6-(1-methylpyrazol-3-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C1=NN(C=C1)C)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(C)O ACOIHWFRGXUVFL-UHFFFAOYSA-N 0.000 claims 1
DXJIISJGBUZPKX-UHFFFAOYSA-N 2-[3-[8-amino-6-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C=1C=NN(C=1)C)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(C)O DXJIISJGBUZPKX-UHFFFAOYSA-N 0.000 claims 1
WWGPBAPYJSIUAN-UHFFFAOYSA-N 2-[3-[8-amino-6-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,3-trifluoropropane-1,2-diol Chemical compound NC=1C=2N(C=C(N=1)C=1C=NN(C=1)C)C(=CN=2)C=1C=C(C=CC=1C)C(CO)(C(F)(F)F)O WWGPBAPYJSIUAN-UHFFFAOYSA-N 0.000 claims 1
PDGNBQKLRTZEED-UHFFFAOYSA-N 2-[3-[8-amino-6-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C=1C=NNC=1)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(C)O PDGNBQKLRTZEED-UHFFFAOYSA-N 0.000 claims 1
SSIGHBGNAKHBJB-UHFFFAOYSA-N 2-[3-[8-amino-6-(2,4-dimethylpyrazol-3-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CN1N=CC(C)=C1C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)F SSIGHBGNAKHBJB-UHFFFAOYSA-N 0.000 claims 1
RQRHRPQMRGHJMM-UHFFFAOYSA-N 2-[3-[8-amino-6-(2,5-dimethylpyrazol-3-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CN1N=C(C)C=C1C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)F RQRHRPQMRGHJMM-UHFFFAOYSA-N 0.000 claims 1
HOIBQUXHBRWEKG-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-cyclopropyl-1,3-thiazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C1=CN=C(S1)C1CC1)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)(F)F)(C)O HOIBQUXHBRWEKG-UHFFFAOYSA-N 0.000 claims 1
LWHKKLDRFTUPNH-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-cyclopropylethynyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C#CC1CC1 LWHKKLDRFTUPNH-UHFFFAOYSA-N 0.000 claims 1
QPBDPIMVYOPVTK-FIBGUPNXSA-N 2-[3-[8-amino-6-(2-hydroxypropan-2-yl)imidazo[1,2-a]pyrazin-3-yl]-4-(trideuteriomethyl)phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C(C)(C)O)C(=CN=2)C=1C=C(C=CC=1C([2H])([2H])[2H])C(C(F)(F)F)(C)O QPBDPIMVYOPVTK-FIBGUPNXSA-N 0.000 claims 1
BRQQUAIYOJTWNU-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-hydroxypropan-2-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,3-trifluoro-2-hydroxypropanamide Chemical compound CC1=C(C=C(C=C1)C(O)(C(N)=O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C(C)(C)O BRQQUAIYOJTWNU-UHFFFAOYSA-N 0.000 claims 1
RDLZUVPSLRGCKB-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-methoxypyridin-3-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound COC1=NC=CC=C1C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)F RDLZUVPSLRGCKB-UHFFFAOYSA-N 0.000 claims 1
RINJEEWRWUKPEI-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-methyl-1,3-oxazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CC1=NC=C(O1)C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)F RINJEEWRWUKPEI-UHFFFAOYSA-N 0.000 claims 1
RQKYFZGSJSHECE-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-methyl-1,3-oxazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,3-trifluoropropane-1,2-diol Chemical compound NC=1C=2N(C=C(N=1)C1=CN=C(O1)C)C(=CN=2)C=1C=C(C=CC=1C)C(CO)(C(F)(F)F)O RQKYFZGSJSHECE-UHFFFAOYSA-N 0.000 claims 1
LBEQXIUDHUFHAL-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-methyl-1,3-thiazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CC1=NC=C(S1)C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)F LBEQXIUDHUFHAL-UHFFFAOYSA-N 0.000 claims 1
USVPZTCVTWNVJK-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-methyl-1,3-thiazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,3-trifluoropropane-1,2-diol Chemical compound NC=1C=2N(C=C(N=1)C1=CN=C(S1)C)C(=CN=2)C=1C=C(C=CC=1C)C(CO)(C(F)(F)F)O USVPZTCVTWNVJK-UHFFFAOYSA-N 0.000 claims 1
GOKAHGXUXLHNAM-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-methylpyrazol-3-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C1=CC=NN1C)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)(F)F)(C(F)(F)F)O GOKAHGXUXLHNAM-UHFFFAOYSA-N 0.000 claims 1
KUSCXKBIHZUXAE-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-methylpyrazol-3-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluorobutan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C1=CC=NN1C)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(CC)O KUSCXKBIHZUXAE-UHFFFAOYSA-N 0.000 claims 1
SIXHPPDTYHQPJH-UHFFFAOYSA-N 2-[3-[8-amino-6-(2-methylpyrazol-3-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C1=CC=NN1C)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(C)O SIXHPPDTYHQPJH-UHFFFAOYSA-N 0.000 claims 1
XJOPBWCPOXABHD-UHFFFAOYSA-N 2-[3-[8-amino-6-(3,5-dimethyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CC1=C(C(C)=NN1)C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)F XJOPBWCPOXABHD-UHFFFAOYSA-N 0.000 claims 1
IBRPDUCSPKZNOI-UHFFFAOYSA-N 2-[3-[8-amino-6-(3-fluoro-2-methylpyridin-4-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C1=C(C(=NC=C1)C)F)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(C)O IBRPDUCSPKZNOI-UHFFFAOYSA-N 0.000 claims 1
IMRLYDSOPDRFCA-UHFFFAOYSA-N 2-[3-[8-amino-6-(3-methyl-1,2-oxazol-5-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C1=CC(=NO1)C)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(C)O IMRLYDSOPDRFCA-UHFFFAOYSA-N 0.000 claims 1
WUZORKHBYODKHM-UHFFFAOYSA-N 2-[3-[8-amino-6-(5-methoxy-1,3-thiazol-2-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1,1-trifluoropropan-2-ol Chemical compound COC1=CN=C(S1)C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)(F)F WUZORKHBYODKHM-UHFFFAOYSA-N 0.000 claims 1
SCSXVNLILPXNDA-UHFFFAOYSA-N 2-[3-[8-amino-6-(5-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CC1=NNC=C1C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)F SCSXVNLILPXNDA-UHFFFAOYSA-N 0.000 claims 1
LRIRQVVVYNRCFJ-UHFFFAOYSA-N 2-[3-[8-amino-6-(5-methylsulfonylpyridin-3-yl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C=1C=NC=C(C=1)S(=O)(=O)C)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(C)O LRIRQVVVYNRCFJ-UHFFFAOYSA-N 0.000 claims 1
MKGRRHINELDJHE-FIBGUPNXSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-(trideuteriomethyl)phenyl]-1,1,1-trifluoro-3-methylbutane-2,3-diol Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C([2H])([2H])[2H])C(C(F)(F)F)(C(C)(O)C)O MKGRRHINELDJHE-FIBGUPNXSA-N 0.000 claims 1
DDHIABQPNCTNPX-FIBGUPNXSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-(trideuteriomethyl)phenyl]-1,1,1-trifluorobutane-2,3-diol Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C([2H])([2H])[2H])C(C(F)(F)F)(C(C)O)O DDHIABQPNCTNPX-FIBGUPNXSA-N 0.000 claims 1
SEFNPZNTENCNMU-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-fluorophenyl]-1,1,1-trifluoropropan-2-ol Chemical compound CC(O)(C1=CC(C2=CN=C3N2C=C(N=C3N)C(F)(F)F)=C(F)C=C1)C(F)(F)F SEFNPZNTENCNMU-UHFFFAOYSA-N 0.000 claims 1
BDQSSGFORSYFMJ-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1,1-trifluoro-4-(methylamino)butan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)(F)F)(CCNC)O BDQSSGFORSYFMJ-UHFFFAOYSA-N 0.000 claims 1
QABGLAMXHIDZGT-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1,1-trifluoro-4-(oxan-4-ylamino)butan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)(F)F)(CCNC1CCOCC1)O QABGLAMXHIDZGT-UHFFFAOYSA-N 0.000 claims 1
INWZFSMORTYESL-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)(F)F)(C)O INWZFSMORTYESL-UHFFFAOYSA-N 0.000 claims 1
LOTLQNANVZIFML-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(C)O LOTLQNANVZIFML-UHFFFAOYSA-N 0.000 claims 1
OUGJFVMAFOQXKZ-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1-chloro-1,1-difluoropropan-2-ol Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)(F)Cl)C1=CN=C2N1C=C(N=C2N)C(F)(F)F OUGJFVMAFOQXKZ-UHFFFAOYSA-N 0.000 claims 1
RLLCLUNILBCDTN-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1-fluoropropan-2-ol Chemical compound CC1=C(C=C(C=C1)C(C)(O)CF)C1=CN=C2N1C=C(N=C2N)C(F)(F)F RLLCLUNILBCDTN-UHFFFAOYSA-N 0.000 claims 1
MWSSHGZSOYDQFI-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,3-trifluoro-2-hydroxy-N-(3-methylazetidin-3-yl)propanamide Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C)C(C(=O)NC1(CNC1)C)(C(F)(F)F)O MWSSHGZSOYDQFI-UHFFFAOYSA-N 0.000 claims 1
OVZMGORTZQEAQS-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,3-trifluoro-2-hydroxy-N-methylpropanamide Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C)C(C(=O)NC)(C(F)(F)F)O OVZMGORTZQEAQS-UHFFFAOYSA-N 0.000 claims 1
QCKJNSZCWZNIOG-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,3-trifluoro-2-hydroxypropanoic acid Chemical compound CC1=C(C=C(C=C1)C(O)(C(O)=O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C(F)(F)F QCKJNSZCWZNIOG-UHFFFAOYSA-N 0.000 claims 1
IANJJQIWXJMBHK-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,3-trifluoropropane-1,2-diol Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C)C(CO)(C(F)(F)F)O IANJJQIWXJMBHK-UHFFFAOYSA-N 0.000 claims 1
HDSBZJKOUWORFQ-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3,4,4,4-pentafluorobutan-2-ol Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)(F)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C(F)(F)F HDSBZJKOUWORFQ-UHFFFAOYSA-N 0.000 claims 1
REQTYLRNIRUPDJ-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-3,3-difluoro-2-hydroxypropanamide Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1C)C(C(=O)N)(C(F)F)O REQTYLRNIRUPDJ-UHFFFAOYSA-N 0.000 claims 1
MNLUURKZLPXCDG-UHFFFAOYSA-N 2-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C=1C=C(C=CC=1)C(C(F)(F)F)(C)O MNLUURKZLPXCDG-UHFFFAOYSA-N 0.000 claims 1
XTPSLLIRSJXXRH-UHFFFAOYSA-N 2-[3-[8-amino-6-[2-(hydroxymethyl)cyclopropyl]imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)F)C1=CN=C2N1C=C(N=C2N)C1CC1CO XTPSLLIRSJXXRH-UHFFFAOYSA-N 0.000 claims 1
LGSPRNFEAYMGNC-UHFFFAOYSA-N 2-[3-[8-amino-6-[2-(hydroxymethyl)pyridin-4-yl]imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C1=CC(CO)=NC=C1 LGSPRNFEAYMGNC-UHFFFAOYSA-N 0.000 claims 1
MATAVIMQKMNSMA-UHFFFAOYSA-N 2-[3-[8-amino-6-[2-(hydroxymethyl)pyridin-4-yl]imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)F)C1=CN=C2N1C=C(N=C2N)C1=CC(CO)=NC=C1 MATAVIMQKMNSMA-UHFFFAOYSA-N 0.000 claims 1
SIXHPPDTYHQPJH-HPRDVNIFSA-N 2-[3-[8-amino-6-[2-(trideuteriomethyl)pyrazol-3-yl]imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C1=CC=NN1C([2H])([2H])[2H])C(=CN=2)C=1C=C(C=CC=1C)C(C(F)F)(C)O SIXHPPDTYHQPJH-HPRDVNIFSA-N 0.000 claims 1
NUTXPEVFWARTGU-UHFFFAOYSA-N 2-[3-[8-amino-6-[3-(hydroxymethyl)cyclobutyl]imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C1CC(CO)C1 NUTXPEVFWARTGU-UHFFFAOYSA-N 0.000 claims 1
VSFUFCFQEFEEAD-FIBGUPNXSA-N 2-[3-[8-amino-6-[6-(1-hydroxyethyl)pyridin-3-yl]imidazo[1,2-a]pyrazin-3-yl]-4-(trideuteriomethyl)phenyl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C=1C=NC(=CC=1)C(C)O)C(=CN=2)C=1C=C(C=CC=1C([2H])([2H])[2H])C(C(F)(F)F)(C)O VSFUFCFQEFEEAD-FIBGUPNXSA-N 0.000 claims 1
QYHPWSNPVYYJRQ-UHFFFAOYSA-N 2-[3-[8-amino-6-[6-(1-hydroxyethyl)pyridin-3-yl]imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CC(O)C1=CC=C(C=N1)C1=CN2C(=CN=C2C(N)=N1)C1=C(C)C=CC(=C1)C(C)(O)C(F)F QYHPWSNPVYYJRQ-UHFFFAOYSA-N 0.000 claims 1
VIRAPALVSMMMIP-UHFFFAOYSA-N 2-[3-[8-amino-6-[6-(hydroxymethyl)pyridin-3-yl]imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-1,1-difluoropropan-2-ol Chemical compound CC1=C(C=C(C=C1)C(C)(O)C(F)F)C1=CN=C2N1C=C(N=C2N)C1=CC=C(CO)N=C1 VIRAPALVSMMMIP-UHFFFAOYSA-N 0.000 claims 1
DTLDMAAXGNTFOQ-UHFFFAOYSA-N 2-[4-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-1-(benzenesulfonyl)indol-6-yl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C=2N(C=C(N=1)C(F)(F)F)C(=CN=2)C1=C2C=CN(C2=CC(=C1)C(C(F)(F)F)(C)O)S(=O)(=O)C1=CC=CC=C1 DTLDMAAXGNTFOQ-UHFFFAOYSA-N 0.000 claims 1
HZIIYHAZBHMQGF-UHFFFAOYSA-N 2-[4-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-5-methylpyridin-2-yl]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=CN=C(C=C1C1=CN=C2N1C=C(N=C2N)C(F)(F)F)C(C)(O)C(F)(F)F HZIIYHAZBHMQGF-UHFFFAOYSA-N 0.000 claims 1
CFEGAWLLXXVCKI-UHFFFAOYSA-N 2-[5-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-2-fluoro-4-methylphenyl]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=CC(F)=C(C=C1C1=CN=C2N1C=C(N=C2N)C(F)(F)F)C(C)(O)C(F)(F)F CFEGAWLLXXVCKI-UHFFFAOYSA-N 0.000 claims 1
IDQFUOQNUKIXCT-UHFFFAOYSA-N 2-[5-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-2-fluorophenyl]-1,1,1-trifluoropropan-2-ol Chemical compound N1=C2N(C(=C1)C1=CC=C(F)C(C(O)(C(F)(F)F)C)=C1)C=C(N=C2N)C(F)(F)F IDQFUOQNUKIXCT-UHFFFAOYSA-N 0.000 claims 1
NAYISRPQBDOZLL-UHFFFAOYSA-N 2-[5-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-6-methylpyridin-3-yl]-1,1,1-trifluoropropan-2-ol Chemical compound CC1=C(C=C(C=N1)C(C)(O)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C(F)(F)F NAYISRPQBDOZLL-UHFFFAOYSA-N 0.000 claims 1
YRYQAKRVSGUMGS-UHFFFAOYSA-N 2-[8-amino-3-[2-methyl-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]-1-morpholin-4-ylethanone Chemical compound NC=1C=2N(C=C(N=1)CC(=O)N1CCOCC1)C(=CN=2)C1=C(C=CC(=C1)C(C(F)(F)F)(C)O)C YRYQAKRVSGUMGS-UHFFFAOYSA-N 0.000 claims 1
HQDNPWGPJIBQII-UHFFFAOYSA-N 2-[8-amino-3-[2-methyl-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]-N,N-dimethylacetamide Chemical compound NC=1C=2N(C=C(N=1)CC(=O)N(C)C)C(=CN=2)C1=C(C=CC(=C1)C(C(F)(F)F)(C)O)C HQDNPWGPJIBQII-UHFFFAOYSA-N 0.000 claims 1
JWUNOCLBEFKXRD-UHFFFAOYSA-N 2-[8-amino-3-[5-(1,1-difluoro-2-hydroxypropan-2-yl)-2-methylphenyl]imidazo[1,2-a]pyrazin-6-yl]-N-(1-hydroxy-2-methylpropan-2-yl)cyclopropane-1-carboxamide Chemical compound NC=1C=2N(C=C(N=1)C1C(C1)C(=O)NC(CO)(C)C)C(=CN=2)C1=C(C=CC(=C1)C(C(F)F)(C)O)C JWUNOCLBEFKXRD-UHFFFAOYSA-N 0.000 claims 1
URIZKMRERIRMGN-UHFFFAOYSA-N 2-[8-amino-3-[5-(1,1-difluoro-2-hydroxypropan-2-yl)-2-methylphenyl]imidazo[1,2-a]pyrazin-6-yl]-N-methylcyclopropane-1-carboxamide Chemical compound NC=1C=2N(C=C(N=1)C1C(C1)C(=O)NC)C(=CN=2)C1=C(C=CC(=C1)C(C(F)F)(C)O)C URIZKMRERIRMGN-UHFFFAOYSA-N 0.000 claims 1
LAFXZKRNVAFLJU-UHFFFAOYSA-N 3-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-4,4,4-trifluoro-3-hydroxy-N,2,2-trimethylbutanamide Chemical compound CNC(=O)C(C)(C)C(O)(C1=CC(C2=CN=C3N2C=C(N=C3N)C(F)(F)F)=C(C)C=C1)C(F)(F)F LAFXZKRNVAFLJU-UHFFFAOYSA-N 0.000 claims 1
HYIIEJPNGKMKNA-UHFFFAOYSA-N 3-[3-[8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-4-methylphenyl]-4,4,4-trifluorobutane-1,3-diol Chemical compound CC1=C(C=C(C=C1)C(O)(CCO)C(F)(F)F)C1=CN=C2N1C=C(N=C2N)C(F)(F)F HYIIEJPNGKMKNA-UHFFFAOYSA-N 0.000 claims 1
YSGFBKUQJGZMNT-FIBGUPNXSA-N 3-[4-[8-amino-3-[2-(trideuteriomethyl)-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]imidazo[1,2-a]pyrazin-6-yl]pyrazol-1-yl]-3-cyclobutylpropanenitrile Chemical compound NC=1C=2N(C=C(N=1)C=1C=NN(C=1)C(CC#N)C1CCC1)C(=CN=2)C1=C(C=CC(=C1)C(C(F)(F)F)(C)O)C([2H])([2H])[2H] YSGFBKUQJGZMNT-FIBGUPNXSA-N 0.000 claims 1
MJUTXXGSBKRFCK-UHFFFAOYSA-N 3-[5-(3-acetamido-1,1,1-trifluoro-2-hydroxypropan-2-yl)-2-methylphenyl]-8-amino-N-ethylimidazo[1,2-a]pyrazine-6-carboxamide Chemical compound CC(=O)NCC(C1=CC(C=2N3C=C(C(=O)NCC)N=C(N)C3=NC=2)=C(C)C=C1)(O)C(F)(F)F MJUTXXGSBKRFCK-UHFFFAOYSA-N 0.000 claims 1
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Classifications

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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Immunology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

ES18797408T 2017-10-18 2018-10-17 Derivados de imidazol condensados sustituidos por grupos hidroxi terciarios como inhibidores de PI3K-gamma Active ES2902390T3 (es)

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US201762608897P	2017-12-21	2017-12-21
US201862727316P	2018-09-05	2018-09-05
PCT/US2018/056311 WO2019079469A1 (fr)	2017-10-18	2018-10-17	Dérivés d'imidazole condensés, substitués par des groupes hydroxy tertiaires, utilisés comme inhibiteurs de pi3k-gamma

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CN (2)	CN111542526B (fr)
AU (2)	AU2018350980C1 (fr)
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CR (2)	CR20200214A (fr)
CY (1)	CY1124814T1 (fr)
EC (1)	ECSP20024651A (fr)
ES (1)	ES2902390T3 (fr)
GE (1)	GEP20237483B (fr)
HR (1)	HRP20211827T1 (fr)
HU (1)	HUE056615T2 (fr)
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JOP20200152A1 (ar)	2017-12-19	2022-10-30	Turning Point Therapeutics Inc	مركبات حلقية كبرى لعلاج مرض
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JOP20200342A1 (ar)	2018-07-05	2020-12-30	Incyte Corp	مشتقات بيرازين مدمجة كمثبطات a2a/a2b
IL309869A (en) *	2018-09-05	2024-02-01	Incyte Corp	Crystal forms of phosphoinositide 3-kinase inhibitor (PI3K)
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US20190152975A1 (en)	2019-05-23
CN111542526B (zh)	2024-01-09
PL3697789T3 (pl)	2022-02-21
HRP20211827T1 (hr)	2022-03-18
IL273983B (en)	2022-10-01
IL295978B2 (en)	2024-01-01
IL273983B2 (en)	2023-02-01
ECSP20024651A (es)	2020-06-30
JOP20200086A1 (ar)	2020-04-30
MA50398A (fr)	2021-05-05
TW201927788A (zh)	2019-07-16
EP4006034A1 (fr)	2022-06-01
AU2018350980C1 (en)	2024-12-12
PT3697789T (pt)	2021-12-31
TWI803525B (zh)	2023-06-01
MA50398B1 (fr)	2021-10-29
SG11202003428VA (en)	2020-05-28
AU2023203088A1 (en)	2023-06-15
WO2019079469A1 (fr)	2019-04-25
KR102717072B1 (ko)	2024-10-15
KR20240152947A (ko)	2024-10-22
US20220213107A1 (en)	2022-07-07
JP2021500340A (ja)	2021-01-07
TW202340200A (zh)	2023-10-16
MX2020003862A (es)	2020-08-13
AU2018350980B2 (en)	2023-02-23
IL295978B1 (en)	2023-09-01
JP2023085290A (ja)	2023-06-20
BR112020007593A2 (pt)	2020-09-24
SA520411783B1 (ar)	2024-05-12
CR20210442A (es)	2021-12-20
CY1124814T1 (el)	2022-11-25
EP3697789B1 (fr)	2021-09-29
US10738057B2 (en)	2020-08-11
EP3697789A1 (fr)	2020-08-26
CL2020001047A1 (es)	2020-08-28
AU2018350980A1 (en)	2020-04-30
JP7541594B2 (ja)	2024-08-28
LT3697789T (lt)	2021-12-10
JP7244504B2 (ja)	2023-03-22
AU2023203088B2 (en)	2024-10-03
SI3697789T1 (sl)	2022-04-29
IL273983A (en)	2020-05-31
US20240228498A1 (en)	2024-07-11
IL295978A (en)	2022-10-01
CR20200214A (es)	2020-07-25
HUE056615T2 (hu)	2022-02-28
PE20210169A1 (es)	2021-01-29
GEP20237483B (en)	2023-03-27
KR20200089264A (ko)	2020-07-24
US20200385392A1 (en)	2020-12-10
CA3084589A1 (fr)	2019-04-25
CN118063470A (zh)	2024-05-24
ZA202201220B (en)	2023-03-29
US11225486B2 (en)	2022-01-18
RS62818B1 (sr)	2022-02-28
US11926630B2 (en)	2024-03-12
TWI834560B (zh)	2024-03-01
CN111542526A (zh)	2020-08-14
UA128085C2 (uk)	2024-04-03
MD3697789T2 (ro)	2022-02-28
PH12020550442A1 (en)	2021-05-31

Publication	Publication Date	Title
ES2902390T3 (es)	2022-03-28	Derivados de imidazol condensados sustituidos por grupos hidroxi terciarios como inhibidores de PI3K-gamma
WO2017223414A1 (fr)	2017-12-28	Composants hétérocycliques utilisés en tant qu'inhibiteurs de pi3k-y
AU2019272342B2 (en)	2024-03-07	Aminopyrazine diol compounds as PI3K-y inhibitors
WO2020102150A1 (fr)	2020-05-22	Dérivés hétérocycliques utilisés comme inhibiteurs de pi3k
WO2020010003A1 (fr)	2020-01-09	DÉRIVÉS D'AMINOPYRAZINE UTILISÉS EN TANT QU'INHIBITEURS DE PI3K-γ
WO2020102198A1 (fr)	2020-05-22	Dérivés hétérocycliques utilisés en tant qu'inhibiteurs de pi3k
EA043981B1 (ru)	2023-07-12	ТРЕТИЧНЫЕ СПИРТЫ В КАЧЕСТВЕ ИНГИБИТОРОВ PI3K-γ
EA045434B1 (ru)	2023-11-24	СОЕДИНЕНИЯ АМИНОПИРАЗИНДИОЛА КАК ИНГИБИТОРЫ PI3Kγ